p-nitrophenyl β-D-xylopyranosyl-(1->4)-β-D-xylopyranoside | 6819-07-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-nitrophenyl β-D-xylopyranosyl-(1->4)-β-D-xylopyranoside
• 英文别名: 4-nitrophenyl-β-D-xylobioside；p-nitrophenyl-β-D-xylobioside；4-nitrophenyl β-xylobioside；4-nitrophenyl-β-D-xylobiose；beta-D-xylopyranoside, 4-nitrophenyl 4-O-beta-D-xylopyranosyl-；(2S,3R,4S,5R)-2-[(3R,4R,5R,6S)-4,5-dihydroxy-6-(4-nitrophenoxy)oxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 6819-07-4
• 化学式: C₁₆H₂₁NO₁₁
• 分子量: 403.343
• InChiKey: LPCFVCUKBNKNBF-DDJMUGOQSA-N

物化性质

• 沸点：
  700.8±60.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  184
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl β-D-xylopyranosyl-(1->4)-β-D-xylopyranoside 在 MES buffer 作用下， 生成 对硝基苯酚
  参考文献：
  名称：

  The Role of Conserved Arginine Residue in Loop 4 of Glycoside Hydrolase Family 10 Xylanases

  摘要：

  糖苷水解酶家族10（GH10）木聚糖酶中，连接β链4和α螺旋4的环4中的精氨酸残基是保守的。来自嗜盐芽孢杆菌C-125的木聚糖酶A（XynA）中的精氨酸残基Arg204和来自粪肠球菌F9的木聚糖酶B（XynB）中的精氨酸残基Arg196被谷氨酸、赖氨酸或谷氨酰胺残基（XynA R204E、K和Q，以及XynB R196E、K和Q）取代。测量了这些突变酶的pH-kcat⁄Km和pH-kcat关系。根据这些曲线计算出的pKe2和pKes2值分别为8.59和8.29（R204E）、8.59和8.10（R204K）、8.61和8.19（R204Q）、7.42和7.19（R196E）、7.49和7.18（R196K）以及7.86和7.38（R196Q）。只有精氨酸衍生物的pKes2值小于野生型（8.49和9.39 [XynA

  DOI：

  10.1271/bbb.69.904
• 作为产物：
  描述：

  4-硝基苯基-BETA-D-吡喃木糖苷 在 吡啶 、 3 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 、 二正丁基氧化锡 、 溶剂黄146 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 3.75h， 生成 p-nitrophenyl β-D-xylopyranosyl-(1->4)-β-D-xylopyranoside
  参考文献：
  名称：

  β-木糖苷的短合成

  摘要：

  摘要苄基2,3,2'，3'，4'-戊-O-乙酰基-β-木糖苷，2-硝基苯基β-木糖苷，4-硝基苯基β-木糖苷和2-碘苄基1-硫代-β-木糖苷通过短而高度选择性的途径合成。使用二丁基氧化锡和三乙基甲硅烷基氯选择性地将β-d-吡喃吡喃糖苷4-O-三乙基甲硅烷基化，然后将2，3-二-O-乙酰化。在酸性条件下进行甲硅烷基化得到4-未保护的木糖苷，然后使用2,3,4-三-O-乙酰基-α-d-木吡喃糖基三氯乙酰亚氨酸酯将其β-d-木糖基化。

  DOI：

  10.1016/0008-6215(94)00214-2

文献信息

• An efficient chemical-enzymatic synthesis of 4-nitrophenyl β-xylobioside: a chromogenic substrate for xylanases
  作者：Adva Mechaly、Valery Belakhov、Yuval Shoham、Timor Baasov

  DOI：10.1016/s0008-6215(97)00209-7

  日期：1997.11

  Abstract 4-Nitrophenyl-β-xylobioside was synthesized by an improved short chemical-enzymatic method, based on the use of xylobiose as a starting material. Xylobiose was prepared following extensive enzymatic digestion of birchwood xylan with xylanase T-6. The resulting digest, containing mainly xylobiose and xylose, was directly subjected to an acetylation step, which after silica gel chromatography

  摘要以木糖为原料，采用改进的短化学酶法合成了4-硝基苯基-β-木糖苷。在用木聚糖酶T-6对桦木木聚糖进行广泛的酶消化之后，制备木糖。将所得的主要包含木糖和木糖的消化物直接进行乙酰化步骤，该步骤在硅胶色谱法后提供高纯度的木糖六乙酸盐。用乙酸中的HBr溴化可定量获得相应的溴化物，在偶联和脱保护步骤后，可得到目标物4-硝基苯基-β-木二糖苷。
• A short synthesis of β-xylobiosides
  作者：Lothar Ziser、Stephen G. Withers

  DOI：10.1016/0008-6215(94)00214-2

  日期：1994.12

  Abstract Benzyl 2,3,2′,3′,4′-penta-O-acetyl-β-xylobioside, 2-nitrophenyl β-xylobioside, 4-nitrophenyl β-xylobioside, and 2-iodobenzyl 1-thio-β-xylobioside were synthesized via a short and highly selective route. β- d -Xylopyranosides were selectively 4-O-triethylsilylated using dibutyltin oxide and triethylsilyl chloride and subsequently 2,3-di-O-acetylated. Desilylation under acidic conditions gave

  摘要苄基2,3,2'，3'，4'-戊-O-乙酰基-β-木糖苷，2-硝基苯基β-木糖苷，4-硝基苯基β-木糖苷和2-碘苄基1-硫代-β-木糖苷通过短而高度选择性的途径合成。使用二丁基氧化锡和三乙基甲硅烷基氯选择性地将β-d-吡喃吡喃糖苷4-O-三乙基甲硅烷基化，然后将2，3-二-O-乙酰化。在酸性条件下进行甲硅烷基化得到4-未保护的木糖苷，然后使用2,3,4-三-O-乙酰基-α-d-木吡喃糖基三氯乙酰亚氨酸酯将其β-d-木糖基化。
• A New Archaeal β-Glycosidase from Sulfolobus solfataricus
  作者：Beatrice Cobucci-Ponzano、Vincenzo Aurilia、Gennaro Riccio、Bernard Henrissat、Pedro M. Coutinho、Andrea Strazzulli、Anna Padula、Maria Michela Corsaro、Giuseppina Pieretti、Gabriella Pocsfalvi、Immacolata Fiume、Raffaele Cannio、Mosè Rossi、Marco Moracci

  DOI：10.1074/jbc.m109.086470

  日期：2010.7

  SSO1353 operates via a retaining reaction mechanism. The catalytic nucleophile (Glu-335) was identified through trapping of the 2-deoxy-2-fluoroglucosyl enzyme intermediate and subsequent peptide mapping, while the general acid/base was identified as Asp-462 through detailed mechanistic analysis of a mutant at that position, including azide rescue experiments. SSO1353 has detectable homologs of unknown

  碳水化合物活性酶 (CAZymes) 是一大类酶，可构建和分解细胞的复杂碳水化合物。根据它们的氨基酸序列，它们被分类为显示保守催化机制、结构和活性位点残基的家族和氏族，但底物特异性可能不同。我们在这里报告了一种新型糖苷水解酶的鉴定和详细的分子表征，该酶由嗜热古菌 Sulfolobus solfataricus 的基因 sso1353 编码。该酶水解芳基 β-葡糖苷和 β-木糖苷，对转木糖基化反应产物的观察表明 SSO1353 通过保留反应机制起作用。催化亲核试剂 (Glu-335) 通过捕获 2-deoxy-2-fluoroglucosyl 酶中间体和随后的肽图鉴定，而一般酸/碱通过对该位置突变体的详细机理分析鉴定为 Asp-462 ，包括叠氮化物拯救实验。SSO1353 在古细菌、细菌和真核生物中具有可检测到的未知特异性的同源物，并且与非溶酶体胆汁酸 β-葡糖苷酶 GBA2（也称为葡糖脑
• Glycosynthase-Mediated Assembly of Xylanase Substrates and Inhibitors
  作者：Ethan D. Goddard-Borger、Brigitte Fiege、Emily M. Kwan、Stephen G. Withers

  DOI：10.1002/cbic.201100229

  日期：2011.7.25

  Assembly by synthase: An exo‐β‐xylosidase mutant with glycosynthase activity greatly simplifies the synthesis of xylanase substrates and inhibitors (see scheme). Some of these glycosynthase products were found to be the most potent competitive inhibitors of glycoside hydrolase family 10 and 11 xylanases reported to date.

  由合酶组装：具有糖合酶活性的exo - β-木糖苷酶突变体大大简化了木聚糖酶底物和抑制剂的合成（请参阅方案）。发现这些糖合酶产物中的一些是迄今为止报道的糖苷水解酶家族10和11木聚糖酶的最有效竞争抑制剂。
• Enzymatic transglycosylation of xylose using a glycosynthase
  作者：Young-Wan Kim、Hongming Chen、Stephen G. Withers

  DOI：10.1016/j.carres.2005.09.010

  日期：2005.12

  The application of the hyperactive glycosynthase derived from Agrobacterium sp. beta-glucosidase (AbgE358G-2F6) to the synthesis of xylo-oligosaccharides by using alpha-D-xylopyranosyl fluoride as donor represents the first successful use of glycosynthase technology for xylosyl transfer. Transfer to beta-nitrophenyl beta-D-glucopyranoside yields di- and trisaccharide products with beta-(1 -> 4) linkages in 63% and 35% yields, respectively. By contrast, transfer to p-nitrophenyl P-D-xylopyranoside yielded the beta-(1 -> 3) linked disaccharide and beta-D-Xyl-(1 -> 4)-beta-D-Xyl-(1 -> 3)-beta-D-Xyl-pNP as major products in 42% and 30% yields, respectively. Transfer of xylose to beta-D-Xyl-(1 -> 4)-beta-D-Xyl-pNP yielded the beta-(1 -> 4) linked trisaccharide in 98% yield, thereby indicating that transfers to xylo-disaccharides occur with formation of beta-(1 -> 4) bonds. Xylosylation of carbamate-protected deoxyxylonojirimycin produced a mixture of di- and tri-'saccharide' products in modest yields. (c) 2005 Elsevier Ltd. All rights reserved.